


Self Care

by DirtyKnots



Series: Kinktober 2017 [30]
Category: Teen Wolf (TV)
Genre: Comeplay, Food Sex, Knotting Dildos, Male Solo, Masturbation, Other, Overstimulation, Pre-Derek Hale/Stiles Stilinski, Sex Toys
Language: English
Status: Completed
Published: 2019-01-29
Updated: 2019-01-29
Packaged: 2019-10-18 23:16:16
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,769
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17590259
Author URL: https://archiveofourown.org/users/DirtyKnots/pseuds/DirtyKnots
Summary: Kinktober 2017 - Day 30: ToysPrompt: my tumblr's down so i am making my request(?) here.. just wanna read some solo derek rn..just derek fucking himself with bananas and cucumbers and popsicles and stuff alone before moving on to dildos and vibes and all that.. lots and lots of depraved derek solo time please - Milan (anon prompt on AO3)





	Self Care

**Author's Note:**

> Special thanks to [pleasurific](https://archiveofourown.org/users/pleasurific) for doing a quick read through and making sure this flowed and also didn't have weird errors. And also motivating me to finish something since I've been in a damn drought lately.

Derek didn't often get much time to himself, but when he did, he made the most of it. The pack was all away at school, Beacon Hills was quiet for once, and the door was bolted from the inside. Derek had shopped just for this, every stray thought and curiosity bought when he realized he'd have time alone. The sun streamed through the loft's giant window pane, illuminating the table he'd set up.

He eyes the knotted dildo he bought, belly tingling in anticipation. It's got a special pump attached so you can fill it up - generally with a synthetic 'come’ that most of the sex shops sell, but Derek's got better plans. Next to it is the brand new milking device he bought, and while it looks odd, he knows it's going to give him exactly what he wants. His cock is already hardening in anticipation, which is just fine with him. Slipping the device on and attaching the catch tube is easier once he's hard, the pressure of it increasing his arousal.

Once he's ready, it's just a matter of getting what he wants so he can fill the knotting dildo up the way he wants - real come that he's going to lock inside himself with that fake knot. While he'd rather have someone else's come, he's not dating at the moment and this is definitely the next best thing. His cock is already drooling into the device attached to it.

There's a smaller array of items on the table as well, things meant to help work himself open, get him ready. He runs his fingers over his options, deciding on a slim vibrator. It's designed to massage the prostate and he thinks that's a good place to start. Derek picks it up, drizzling lube over it and smearing it around before kneeling up on his sofa, reaching back with the toy and running it up and down his crack. He flicks the power on low and shudders when it rumbles against his pucker. He's relaxed enough from his prep in the shower to start teasing himself with the pressure, pressing it more firmly against his hole, not quite breaching himself with it. Already, the vibrations are making his cock leak faster, a steady trickle of precome filling the bottom of the collection tube.

Derek gasps out when he finally stops playing and pushes the toy past his rim, feeling the vibrations against his insides. He's grateful for the reach of the toy, slipping it deeper with ease, massaging himself from the inside. He fucks it in and out a few times, hips rocking back into the thrusts, before angling it a little better and sliding it in to his fingertips, moaning as the vibrations rub and dance across his prostate. It's not quite enough though, so he thumbs the power switch, turns it on high, and then collapses against the back of the sofa, cock twitching and spitting out his first release into the collection tube, free hand spasming in the cushions.

It quickly becomes too much, but it takes him several minutes to regain enough sense to thumb off the power, the pressure against his prostate and from the device over his cock drawing out his orgasm, milking every last spurt of come from him. He's twitching and groaning as he slips the vibrator free, hole spasming once it's empty. He drops the toy to the floor and just lays there, body curled oddly over the sofa while he comes down from his release. The tube meant to collect his come is only a third of the way full when he regains enough sense to check, but that's okay, he's got hours to get himself ready. He's loose and relaxed now, though his legs feel a bit wobbly when he stands and spins back to the table. His cock is still soft, but he isn't overly worried about it as he scans the selection. He could play with another dildo, he's got a few, but he feels the surge of want in his belly when he spies the cucumber. It's maybe a bit bigger than he'd planned on going next, but he feels ready. Relaxed.

Derek picks up the vegetable and settles himself back onto the sofa, legs bent and feet propped on the coffee table, away from the array of toys and foods. He scoots down until his ass is hanging over the edge, brings the cucumber up to his mouth to suck on it, imagining it's a cock and not just something he snatched from his vegetable tray. His mouth waters enough to coat it, and between that and the lube he'd filled himself with already, he thinks it's enough. His free hand thumbs at his nipples when he slides the other down, feeling the wet trails of spit it leaves behind. It's cool against his cock as it moves past, and then it's down at his hole. He runs the tip of it around in slow circles, feeling the way his body twitches involuntarily at the cool touch. It isn't long before he's teasing his opening with it, applying just enough pressure to feel it before backing off. Derek's cock is waking back up under the attention, his hips hitching slightly with each gentle push, toes beginning to curl when he finally breaches himself. It's a lot, more than he'd expected even looking at the girth - though it's nothing close to the dildo he's aiming for today. He only pushes in a bit before he stops, waits while his body adjusts. His rim clings when he drags it back out just as carefully until only the barest bit is holding him open, then begins the steady push back inside.

It doesn't take long at all for Derek to get a rhythm going, thrusting the cucumber as deep as he can, his fingers bumping against his ass before he tightens his grip and pulls it back out. He shifts minutely on the sofa until the angle is right, each thrust pushing the end of the veggie into his prostate. It's not as much stimulation as the massager had given him, but it's enough. He's shaking and shuddering by the time his cock starts spitting, adding to the come he's collecting. He doesn't drag this out right away either, instead letting his arms fall limply to his sides, enjoying the way he's stretched open around the cucumber. His hole keeps clenching and relaxing, and he likes the way he can't close up completely, the way he feels full. It's still not exactly enough, but fuck if it doesn't feel good. It tempts him to go crazier, to find something even fatter, more than the knotting dildo. But not today. He's got a plan.

When he finally feels recovered again, he bears down, enjoys the slow slide of the cucumber as it slips free of his body. He sets it aside and looks at his options, taking a moment to check the tube, a pleased hum escaping when he sees it's over half full. He thinks about his options, thinks about his plans, and selects several carrots, rinsed and ready. He doesn't spend as much time sucking on them to get them even wetter, can feel the way his hole is loose enough to take them even without anything else. He kneels on the floor this time, chest pressed up against the sofa, and pushes them in, one after the other. There's only a few, and he laments that he didn't properly compare them to the thickness of some of his other choices, but his eyes land on the prostate massager again. It's no choice really, there's more than enough stretch in his ass to slide it in alongside the carrots, to wedge it against his prostate and flick it on. He's careful not to jostle it out of place when he grips the ends of the carrots and begins rising up and down on his knees, fucking back onto them. It takes less time for him to come, the constant steady thrum from the massager sending him straight to the end. He doesn't get much more out of his cock, not after coming three times in under two hours, but it's okay, it was enough. The carrots get pulled out quickly, the massager dropping back to the floor on it's own when they're free. 

Derek winces when he pulls the milking tube off of his cock, his body beyond sensitive despite not having touched it at all. It flops, soft and sticky, against his thigh as he turns to empty the tube into the come pump for the dildo. He thinks, briefly, about saving this for another time. There's no way he'll be able to get off again, not for a good long while, but he doesn't want to stop. Not really anyhow. The idea that he'll be able to finally feel what he's been craving for so long is too great. He does, however, make some concessions to the fact that he's likely going to be too exhausted to do much of anything when he finally gets his prize. He rolls the toys - both used and not - into a towel and tosses them into the master bathroom. When that's done, he grabs the carrots and the cucumber and moves to the kitchen, quickly slicing them up and tossing them into a makeshift salad. He only spares a minute to laugh at himself - tossing a salad with ass veggies...he's been spending too much time with Stiles probably. Once they're done, he adds a few other things - tomatoes, mushrooms, a little bit of his own come as dressing - and puts it into a tupperware container clearly marked as his. Generally, nobody eats his salads, so he figures it's safe. Especially since everyone is supposed to be gone until tomorrow. He snatches up a couple bottles of water and then moves to the living room, eyes zeroed in on the last bit of his fun - the knotted dildo, waiting in all its glory, reservoir filled with his own seed.

Derek is careful when he picks it up and moves it to his bedroom - he doesn't want to drop it or spill anything. It's good, he makes it with no problem. It gets set on the nightstand alongside the water bottles while he snatches up his lube. He's pretty open but he doesn't want to risk any pain when he inflates the knot - just because he can heal it doesn't mean he wants to have to. It's an exercise in patience to stretch himself properly, his fingers methodical as they twist and spread inside his hole. He works himself up to four before his wrist twinges and he accepts that he's as open as he can get without more help. He runs his slick hand over the dildo, adding more lube until it's glistening and dripping with it. It takes him a minute after that to decide how he wants to do it, whether he wants to be on his back or on all fours, or just up on his knees. He finally settles on the latter, shifting around on the bed so he can brace himself on his headboard, control for the pump snaked up between his legs, settled just in front of his knees. The dildo is weighted, and the added fullness of the reservoir help keep it upright and in place as he sinks down on it.

Despite how stretched he is, Derek still feels the way his body blooms open around the head of the fake cock, can feel the brush of it against his inner walls as he slides further and further down until the fake balls on the base are pushing against his ass. He wishes he had the real thing - but this is a fairly decent second. He stills, lets his body adjust to the new level of fullness before rising back up. It's slow at first, giving himself time to get used to the stretch, but it doesn't take long for him to start whimpering each time he drops down, speeding up. Derek has the briefest thought that he should invest in something to hold his toys for him, because holding the base himself takes away a little, not being able to just ride the dildo like he would a cock. It's okay though, it's getting the job done. 

The knotting dildo is angled so that it strikes his prostate almost every time he drops down onto it. It bring tears to his eyes, his body so beyond overstimulated, but he doesn't want to stop. Instead he thumbs the valve to start inflating the knot, groaning at the way it stretches his hole even further. The lube in his ass squelches, his body popping off the knot until suddenly it's a struggle to shove back down around it. It's a lot, even with his prep, but Derek just moans when he finally manages to wriggle down onto it, feeling the way his hole clamps down, the extra pressure it exerts on his insides. He can't stop himself from squeezing his ass, feeling the way it shifts the toy inside of him. It's definitely not going anywhere so he's free to release the base, slide his fingers up to feel where it's speared inside of him. 

He keeps his fingers pressed tight to where his ass has swallowed the toy as the thumbs the button that will push his come out of the reservoir and inside of him. His come is cooler than he expects, he can feel the way it's splashing up into him, filling him. Another squeeze of his ass and he can feel tiny trails of it slipping free where he's spread around the dildo, groans and tips himself sideways as the reservoir empties into him. His cock gives a half-hearted twitch but he's still too spent, wishes though that he could get off one last time now that he's finally full. It's not exactly what he wanted, but it's close enough for now.

He doesn't fight it when he starts to drift, the toy still locked tight inside of him, keeping him full of his own come. He knows he should clean himself up, clean up the loft. Eat something. But he's not ready to be empty yet. Instead he falls asleep where he's at, content if not entirely satisfied.

When Derek wakes, it's to the sound of someone else moving around in the loft. It takes him a minute to orient himself, to remember where he is and what he'd been doing. The toy is still inside him, and he can hear the hiss as he hits the release valve to shrink the fake knot. His come slides out as the toy shrinks, despite his healing kicking in to tighten him up. He wishes that he'd cleaned up already, hopes it isn't one of his betas downstairs. He throws on loose shorts and a tank top and moves to the staircase, slips down them quietly. He sucks in a sharp breath when he finally gets to the kitchen and finds Stiles sitting at the bar, digging into the salad he'd clearly marked as his own, making happy little noises as he eats.

“Derek! How's it going oh alpha my alpha?”

“Stiles...what are you doing here? Aren't you supposed to be in class?”

“Cancelled. Figured I'd get an early weekend. Dad's at work, everyone else is gone. I called but you didn't answer.”

“So you let yourself in and decided to eat my food?” Derek can feel the blush creeping over his skin as he watches Stiles' take another bite, carrot and cucumber crunching between his teeth.

“I haven't seen a salad in a month. Sorry man. But also,this is delicious. You gotta tell me what dressing you use, I think even my dad would enjoy this.” Derek can't stop himself from choking as soon as the words slip out of Stiles’ mouth.

“I really, really doubt that.” Derek's face feels like it's on fire, and Stiles’ brow furrows.

“Why not?” Derek just stares, can't answer, face burning, until Stiles sets down the container and his fork, looking between the dish and Derek. “What?”

Derek's head shakes and he slumps down.

“Uh...we should maybe talk.” It's mumbled into his arms where he's dropped his face onto them, but he knows Stiles understood him. He doesn't want to have this conversation, at all, but he has to. He takes a breath and lifts his head and tries to sort out where to start.

**Author's Note:**

> Come find me on [DreamWidth](https://dirtyknots.dreamwidth.org/), all of my additional contact information can be found there or on my [Profile Page](https://archiveofourown.org/users/DirtyKnots/profile) here (including where you can leave me prompts of your own)!


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